Dresses with grown-up hemlines, super-challenging winter edition


I never wear dresses this time of year unless there’s a special occasion of some sort, because—as I have remarked many times—I hate being cold, and even the warmest tights aren’t warm enough (though these look promising). And also, dresses are so rarely well-fabricated for wearing in the winter months. But you can improvise, and the trick is to layer: with a thin long-sleeved tee or turtleneck underneath (this doesn’t work with all dresses, but you’d be surprised at how many it does work with) and a cardigan over, something body-skimming so you don’t lose the shape of the dress. I like this APC dress because it has actual long sleeves, which is all too rare in the dress universe, and a nice relaxed fit.

This Rachel Comey pencil dress is so totally office-perfect, but I’d wear it to a party too.

See what I mean about layering with turtlenecks? I think this look is aces (although I might swap out the embellished sneakers here for a simple black bootie).

This is a pretty obvious—let’s say homage to an Ulla Johnson dress from a few seasons ago, but it’s a ton cheaper.

The slit here keeps this dress from coming off too preppy, and instead skews it appealingly modish.

I really dig the smocking here.

Just a simple black satin dress for throwing on whenever nothing else in your closet seems quite right.

I’d definitely wear this pretty floral number with a long-sleeved tee underneath.

Ribbed cotton makes this one subtly sexy and very wearable.

I do love a floral with a dark background, and the shape here is so appealingly clean.

More pretty smocking, and a nicely flowy silhouette.

This has a big open slit in the back, which I never like to see, but if you wore it with a cardigan, nobody would be the wiser. Or you could go for a set of these.

A spiff leather dress that costs a lot less than most leather dresses, while still being not exactly cheap. Dare I say there is something 1970s YSL about the shape? Probably I’ve got that wrong, but it does feel quite French and of that decade to me. Come after me, fashion historians.

I’d butch up this pleated dress by wearing it with big clunky knee-high boots.



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9 Thoughts on Dresses with grown-up hemlines, super-challenging winter edition
    29 Jan 2019

    The Rixo with a tee or turtle under it would be cool, and I would be crazy for the Equipment dress minus the big open slit in the back (What were they thinking?). I don’t care if they’re “in” or not, but my winter signature dress is a wool blend long-sleeve sheath from Black Crane. Pull on the tights, booties, and some cool earrings and mic drop….outfit done!


    29 Jan 2019

    Ha! I bought that & Other Stories orange dress over the Dec. holidays when I was home in NY visiting family. I can attest it totally rocks and is a STEAL for the price. OK, I have to say, Kim, this is the first time you’ve picked something I picked– I feel like such a fashionista!


    28 Jan 2019

    That orange dress doesn’t look at all preppy to me, in fact it reminds me of a dress I owned in 1970, when my completely hippie boarding school (Northern California) had a dinner dress code. Mine was a cadet blue, but, exact same styling so I will always see this kind of look as a seventies style.


    28 Jan 2019

    I love dresses – no need to worry about matching/having something else clean or having to wake up early enough to look for said – sometimes VERY elusive – matching/clean items, and plan to stop by & Other Stories on my way home in search of the black silk one! Wish this was a muli-parter, but thanks!


    28 Jan 2019

    Amen on the sleeves and the warm problem!

    And can we talk about why retailers* selling dresses in winter show them with such distinctly anti-wintery styling? Open-toed shoes, sandals, no tights or even socks, none of the layering shirts, or anything resembling anything that an actually existing person would need not to freeze in winter? It’s like they think only Floridians need dresses.

    * With the notable exception of LL Bean, because well, LL Bean


    28 Jan 2019

    A big yes to trying fleece lined tights if you live in a colder climate! For reference, I walk to work in winter temperatures that are as cold as those found in Minnesota or Alaska. Fleece lined tights (and a good winter jacket) allow me to wear skirts and dresses all year.


    Nelson Bartley
    28 Jan 2019

    The most unlikely dress but I wish it came in navy and red and maybe a stripe. I have both the black and the gray and wear them dressed up and down. With a belt, without. The fabric is very yummy and surprisingly warm and washes and dries beautifully with no shrinking. And def can’t beat the price…. No incentive to post other than I love this dress and wish it came in a Vneck and other colors….


    28 Jan 2019

    A friend wore the Ganni smocked dress to work last week and I wanted to steal it from her. So, so, so pretty. But sadly, not in my budget.


    28 Jan 2019

    These are all lovely wearable options! Just yesterday I observed a woman of a certain age dressed in something that looked like she borrowed it from her teenage daughter. I know we’re supposed to wear whatever we want and f%&k anyone’s opinion, but sometimes a high hemline on older legs just makes me cringe….



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Kim France

I was born in Houston, Texas in 1964 and have lived in New York City since 1988. I had a long career in magazines, working at Sassy, Elle, New York, and Spin, and in 2000, I founded Lucky magazine, which I edited for ten years.

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